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organic compounds
5-(1H-Tetrazol-5-yl)-1H-indole monohydrate
aSchool of Biological and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, People's Republic of China, and bJiangsu University Environment Engineering, Inc., Zhenjiang, Jiangsu 212003, People's Republic of China
*Correspondence e-mail: cxwchem@yahoo.com.cn
In the title compound, C9H7N5·H2O, the interplanar angles between the benzene and tetrazole rings and between the benzene and imidazole rings are 8.71 (3) and 1.32 (2)°, respectively. In the crystal, strong N—H⋯N hydrogen bonds link the organic 5-(1H-tetrazol-5-yl)-1H-indole molecules into chains extended along the b axis. The chains are further interconnected into layers parallel to (100) via strong O—H⋯N and N—H⋯O hydrogen bonds. Furthermore, the layers are interconnected via strong O—H⋯N hydrogen bonds. Moreover, cohesion between the layers is provided by the π–π interactions between the imidazole, tetrazole and benzene rings with centroid–centroid distances of 3.766 (2), 3.832 (2) and 3.733 (2) Å.
Related literature
For applications of tetrazole derivatives, see: Jin et al. (1994); Fu et al. (2009
). For their use in the synthesis of metal-organic frameworks, see: Brewis et al. (2003
). For related structures, see: Zhao et al. (2008
); Fu et al. (2009
). For the classification of hydrogen bonds, see: Desiraju & Steiner (1999
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536811018575/fb2235sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811018575/fb2235Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811018575/fb2235Isup3.cml
5-(1H-tetrazol-5-yl)-1H-indole was obtained commercially from Alfa Aesar. Colourless block-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol/water (2:1 v/v) solution.
All the H atoms were discernible in the difference electron density maps. All the H atoms attached to the C atoms were situated into the idealized positions and treated as riding with C–H = 0.93 Å with Uiso(H)=1.2Ueq(C). The positional parameters of the H atoms involved in the hydrogen bonds were refined either freely (N1, N5) or as restrained (Ow). The restraints regarded the distances between the water oxygens and the water hydrogens (0.82 (2)Å) while the H1WA—O1w—H1WB angle was set to 105(1.5)°. The constraints regarding the displacement parameters of the amine and water hydrogens: Uiso(H)=1.2Ueq(N); Uiso(H)=1.5Ueq(Ow). Since there has been no significant anomalous scatterer in the structure, 889 Friedel pairs have been merged.
Data collection: CrystalClear (Rigaku, 2005); cell
CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C9H7N5·H2O | F(000) = 424 |
Mr = 203.21 | Dx = 1.434 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1258 reflections |
a = 6.8978 (14) Å | θ = 3.3–27.5° |
b = 9.953 (2) Å | µ = 0.10 mm−1 |
c = 13.713 (3) Å | T = 298 K |
V = 941.4 (3) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
Rigaku Mercury2 diffractometer | 1258 independent reflections |
Radiation source: fine-focus sealed tube | 971 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ϕ scans | h = −8→8 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −12→12 |
Tmin = 0.89, Tmax = 0.95 | l = −17→17 |
9741 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.0295P] where P = (Fo2 + 2Fc2)/3 |
1258 reflections | (Δ/σ)max < 0.001 |
148 parameters | Δρmax = 0.19 e Å−3 |
3 restraints | Δρmin = −0.15 e Å−3 |
24 constraints |
C9H7N5·H2O | V = 941.4 (3) Å3 |
Mr = 203.21 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.8978 (14) Å | µ = 0.10 mm−1 |
b = 9.953 (2) Å | T = 298 K |
c = 13.713 (3) Å | 0.40 × 0.30 × 0.20 mm |
Rigaku Mercury2 diffractometer | 1258 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 971 reflections with I > 2σ(I) |
Tmin = 0.89, Tmax = 0.95 | Rint = 0.069 |
9741 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 3 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.19 e Å−3 |
1258 reflections | Δρmin = −0.15 e Å−3 |
148 parameters |
Experimental. The distance between the sample and the detector is 55 mm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.1423 (4) | 1.0672 (2) | 0.40317 (17) | 0.0433 (6) | |
H1 | 0.144 (5) | 1.145 (3) | 0.433 (2) | 0.052* | |
N5 | 0.1331 (4) | 0.4891 (2) | 0.61965 (15) | 0.0371 (5) | |
H5 | 0.120 (4) | 0.532 (3) | 0.6781 (19) | 0.045* | |
C2 | 0.1601 (4) | 0.6777 (2) | 0.49991 (17) | 0.0296 (6) | |
C3 | 0.1565 (4) | 0.7101 (2) | 0.40154 (17) | 0.0339 (6) | |
H3 | 0.1578 | 0.6428 | 0.3545 | 0.041* | |
C7 | 0.1607 (4) | 0.7798 (3) | 0.57174 (18) | 0.0357 (6) | |
H7 | 0.1637 | 0.7561 | 0.6373 | 0.043* | |
N4 | 0.1313 (4) | 0.3538 (2) | 0.61809 (16) | 0.0456 (6) | |
C5 | 0.1512 (4) | 0.9450 (2) | 0.44822 (18) | 0.0339 (6) | |
N3 | 0.1556 (4) | 0.3203 (2) | 0.52735 (17) | 0.0471 (6) | |
C8 | 0.1406 (5) | 0.9156 (3) | 0.28329 (19) | 0.0441 (7) | |
H8 | 0.1375 | 0.8770 | 0.2215 | 0.053* | |
C1 | 0.1569 (4) | 0.5364 (2) | 0.52883 (18) | 0.0308 (6) | |
C4 | 0.1510 (4) | 0.8459 (2) | 0.37392 (18) | 0.0334 (6) | |
C6 | 0.1569 (4) | 0.9126 (2) | 0.54653 (18) | 0.0362 (6) | |
H6 | 0.1582 | 0.9794 | 0.5940 | 0.043* | |
C9 | 0.1359 (5) | 1.0484 (3) | 0.3040 (2) | 0.0471 (7) | |
H9 | 0.1294 | 1.1169 | 0.2579 | 0.056* | |
N2 | 0.1706 (4) | 0.4307 (2) | 0.47002 (16) | 0.0421 (6) | |
O1W | 0.1242 (4) | 0.6288 (2) | 0.79322 (13) | 0.0541 (6) | |
H1WA | 0.183 (4) | 0.606 (3) | 0.8404 (19) | 0.081* | |
H1WB | 0.045 (4) | 0.683 (3) | 0.806 (2) | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0523 (14) | 0.0299 (11) | 0.0477 (14) | −0.0015 (15) | 0.0014 (13) | −0.0001 (10) |
N5 | 0.0484 (14) | 0.0301 (11) | 0.0328 (12) | −0.0004 (11) | 0.0015 (13) | −0.0005 (10) |
C2 | 0.0271 (13) | 0.0275 (12) | 0.0344 (13) | −0.0007 (13) | 0.0031 (13) | −0.0015 (9) |
C3 | 0.0377 (14) | 0.0327 (13) | 0.0312 (13) | −0.0018 (14) | −0.0009 (13) | −0.0034 (11) |
C7 | 0.0409 (15) | 0.0368 (14) | 0.0292 (12) | −0.0006 (15) | 0.0005 (13) | −0.0012 (11) |
N4 | 0.0628 (15) | 0.0275 (12) | 0.0466 (14) | 0.0006 (13) | 0.0021 (15) | 0.0031 (10) |
C5 | 0.0290 (12) | 0.0279 (12) | 0.0447 (15) | 0.0000 (14) | 0.0015 (12) | −0.0013 (11) |
N3 | 0.0662 (16) | 0.0301 (12) | 0.0450 (14) | −0.0044 (14) | 0.0075 (15) | −0.0014 (10) |
C8 | 0.0552 (18) | 0.0421 (17) | 0.0349 (15) | −0.0046 (16) | −0.0009 (15) | 0.0029 (12) |
C1 | 0.0299 (13) | 0.0295 (13) | 0.0331 (13) | −0.0031 (13) | 0.0006 (13) | −0.0035 (11) |
C4 | 0.0289 (12) | 0.0355 (14) | 0.0359 (14) | −0.0013 (13) | 0.0009 (14) | −0.0039 (11) |
C6 | 0.0449 (15) | 0.0298 (14) | 0.0338 (14) | 0.0019 (14) | −0.0015 (14) | −0.0079 (10) |
C9 | 0.0540 (18) | 0.0397 (15) | 0.0475 (17) | 0.0002 (18) | 0.0029 (16) | 0.0124 (13) |
N2 | 0.0601 (16) | 0.0291 (11) | 0.0370 (12) | −0.0023 (13) | 0.0048 (12) | −0.0025 (10) |
O1W | 0.0737 (17) | 0.0559 (14) | 0.0327 (10) | 0.0169 (13) | −0.0053 (11) | −0.0024 (10) |
N1—C5 | 1.366 (3) | N4—N3 | 1.299 (3) |
N1—C9 | 1.373 (3) | C5—C6 | 1.387 (4) |
N1—H1 | 0.87 (3) | C5—C4 | 1.418 (3) |
N5—C1 | 1.341 (3) | N3—N2 | 1.354 (3) |
N5—N4 | 1.347 (3) | C8—C9 | 1.353 (4) |
N5—H5 | 0.91 (3) | C8—C4 | 1.425 (4) |
C2—C3 | 1.387 (3) | C8—H8 | 0.9300 |
C2—C7 | 1.415 (3) | C1—N2 | 1.329 (3) |
C2—C1 | 1.462 (3) | C6—H6 | 0.9300 |
C3—C4 | 1.403 (3) | C9—H9 | 0.9300 |
C3—H3 | 0.9300 | O1W—H1WA | 0.797 (17) |
C7—C6 | 1.367 (3) | O1W—H1WB | 0.792 (17) |
C7—H7 | 0.9300 | ||
C5—N1—C9 | 109.1 (2) | N4—N3—N2 | 111.0 (2) |
C5—N1—H1 | 125.4 (19) | C9—C8—C4 | 107.1 (2) |
C9—N1—H1 | 125.5 (19) | C9—C8—H8 | 126.5 |
C1—N5—N4 | 109.7 (2) | C4—C8—H8 | 126.5 |
C1—N5—H5 | 131.5 (18) | N2—C1—N5 | 107.1 (2) |
N4—N5—H5 | 118.9 (18) | N2—C1—C2 | 126.6 (2) |
C3—C2—C7 | 120.7 (2) | N5—C1—C2 | 126.2 (2) |
C3—C2—C1 | 119.2 (2) | C3—C4—C5 | 118.4 (2) |
C7—C2—C1 | 120.1 (2) | C3—C4—C8 | 134.8 (2) |
C2—C3—C4 | 119.1 (2) | C5—C4—C8 | 106.7 (2) |
C2—C3—H3 | 120.4 | C7—C6—C5 | 118.1 (2) |
C4—C3—H3 | 120.4 | C7—C6—H6 | 120.9 |
C6—C7—C2 | 121.2 (2) | C5—C6—H6 | 120.9 |
C6—C7—H7 | 119.4 | C8—C9—N1 | 109.9 (2) |
C2—C7—H7 | 119.4 | C8—C9—H9 | 125.1 |
N3—N4—N5 | 105.7 (2) | N1—C9—H9 | 125.1 |
N1—C5—C6 | 130.4 (2) | C1—N2—N3 | 106.5 (2) |
N1—C5—C4 | 107.1 (2) | H1WA—O1W—H1WB | 111 (2) |
C6—C5—C4 | 122.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3i | 0.87 (3) | 2.18 (3) | 3.042 (3) | 171 (3) |
O1W—H1WA···N2ii | 0.80 (2) | 2.08 (2) | 2.869 (3) | 173 (3) |
O1W—H1WB···N4iii | 0.79 (2) | 2.33 (2) | 3.098 (3) | 164 (3) |
N5—H5···O1W | 0.91 (3) | 1.85 (3) | 2.757 (3) | 173 (3) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, −y+1, z+1/2; (iii) −x, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C9H7N5·H2O |
Mr | 203.21 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 6.8978 (14), 9.953 (2), 13.713 (3) |
V (Å3) | 941.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Rigaku Mercury2 diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.89, 0.95 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9741, 1258, 971 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.105, 1.06 |
No. of reflections | 1258 |
No. of parameters | 148 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.15 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3i | 0.87 (3) | 2.18 (3) | 3.042 (3) | 171 (3) |
O1W—H1WA···N2ii | 0.797 (17) | 2.076 (19) | 2.869 (3) | 173 (3) |
O1W—H1WB···N4iii | 0.792 (17) | 2.33 (2) | 3.098 (3) | 164 (3) |
N5—H5···O1W | 0.91 (3) | 1.85 (3) | 2.757 (3) | 173 (3) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, −y+1, z+1/2; (iii) −x, y+1/2, −z+3/2. |
Acknowledgements
This work was supported by a start-up grant from Jiangsu University of Science and Technology, China.
References
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The tetrazole functional derivatives have found a wide range of applications in coordination chemistry as ligands (Fu et al., 2009), in medicinal chemistry as metabolically stable surrogates for the carboxylic acid group (Fu et al., 2009) and in materials science as highly energetical materials for production of tetrazole explosives (Jin et al., 1994). For the varying ability of the tetrazoles to coordinate metal ions, a large number of novel metal-organic frameworks have been synthesized (Brewis et al., 2003). As extension of these works, we report here the crystal structure of the title compound, 5-(1H-tetrazol-5-yl)-1H-indole hydrate.
The interplanar angles between the benzene and the tetrazole and the benzene and imidazole rings equal to 8.71 (3)° and 1.32 (2)°, respectively. The geometric parameters of the tetrazole ring are comparable to those in the related molecules (Zhao et al., 2008; Fu et al., 2009).
The molecular packing is stabilized by strong intermolecular N—H···O, N—H···N and O—H···N hydrogen bonds (the classification of the hydrogen bonds is according to Desiraju & Steiner, 1999). The H-bonds link the molecules into a three-dimensional network (Fig. 2 and Tab. 1). In a more detail, N1-H1···N3 connects the molecules into chains extended along the b-axis. These chains are interconnected by the hydrogen bonds O1W—H1WA···N2 and N5—H5···O1W, forming thus layers parallel to (1 0 0) - see Fig. 2 and Tab. 1. The hydrogen bond O1W—H1WB···N4 interconnects the layers.
The layers are also connected by the π-electron ring··· π-electron ring interactions. The centroid—centroid distances are Cg1—Cg2 (1 + x, y, z) = 3.766 (2) Å; Cg1—Cg2 (1/2 + x, 3/2 - y, 1 - z) = 3.832 (2)Å and Cg3—Cg3 (1/2 + x, 3/2 - y or -1/2 + x, 3/2 - y, 1 - z) = 3.733 (2) Å , where Cg1, Cg2 and Cg3 are the centroids referring to the imidazole, tetrazole and the benzene rings, respectively.